Hydrochloric Acid → HCID 68278059, compound

HRID 931520Notes

Reaction equation

HRID 931520 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][NH:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[O:20][C:21]([CH3:41])=[C:22]([CH2:24][S:25]([CH:28]4[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]4)(=[O:27])=[O:26])[N:23]=3)=[CH:15][CH:14]=2)=[O:12])[CH:3]=1.[OH-].[Na+].O>ClCCl>[CH3:41][C:21]1[O:20][C:19]([C:16]2[CH:15]=[CH:14][C:13]([C:11]([NH:10][CH2:9][CH2:8][C:4]3[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=3)=[O:12])=[CH:18][CH:17]=2)=[N:23][C:22]=1[CH2:24][S:25]([CH:28]1[CH2:29][CH2:30][NH:31][CH2:32][CH2:33]1)(=[O:27])=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 68278093HCID 68278093, compound

Product 1

HCID 68278059HCID 68278059, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Excess hydrogen chloride gas was bubbled into a solution of tert-butyl 4-((2-(4-((2-(pyridin-3-yl)ethyl)carbamoyl)phenyl)-5-methyloxazol-4-yl)methylsulfonyl)piperidine-1-carboxylate (840 mg, 1.48 mmol, 1.00 equiv) in dichloromethane (20 mL) maintained at 0° C. in a water/ice bath. The reaction mixture was stirred at 0° C. for another 2 h. The pH value of the solution was adjusted to 10 with 1M sodium hydroxide solution. Water (400 mL) was then added and the resulting solution was extracted with 5×200 mL of dichloromethane. The combined organic layers was washed with 2×600 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 420 mg (61%) of 4-(5-methyl-4-((piperidin-4-ylsulfonyl)methyl)oxazol-2-yl)-N-(2-(pyridin-3-yl)ethyl)benzamide as a white solid. LC-MS: (ES, m/z): 469 [M+H]+, 320, 235. 1HNMR (400 MHz, CD3OD, ppm) δ 8.47 (s, 1H), 8.42-8.40 (d, 1H), 8.09-8.07 (d, 2H), 7.90-7.88 (d, 2H), 7.81-7.79 (d, 1H), 7.42-7.39 (t, 1H), 4.45 (s, 2H), 3.70-3.66 (t, 2H), 3.43-3.39 (m, 3H), 3.03-2.99 (t, 2H), 2.88-2.82 (m, 2H), 2.50 (s, 3H), 2.34-2.31 (d, 2H), 1.91-1.88 (m, 2H).

Workup

  1. extractionthe resulting solution was extracted with 5×200 mL of dichloromethane
  2. washThe combined organic layers was washed with 2×600 mL of brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-274085964b1a403db724ad98262442ff
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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